Density Functional Theory Calculations of the Molecular Force Field of l -Ascorbic Acid, Vitamin C

Autores
Bichara, Laura Cecilia; Lanús, Hernán Enrique; Nieto Peñalver, Carlos Gabriel; Brandan, Silvia Antonia
Año de publicación
2010
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
We have studied l-ascorbic acid and characterized it by infrared spectroscopy in solid and aqueous solution phases. The density functional theory (DFT) method together with Pople’s basis set show that three stable molecules for the compound have been theoretically determined in the gas phase, and that an average of only two more stable conformations are present in the solid phase, as it was experimentally observed. The harmonic vibrational wavenumbers for the optimized geometries of both structures were calculated at B3LYP/6-31G*and B3LYP/6-311++G** levels at the proximity of the isolated molecule. For a complete assignment of the vibrational spectra in the compound solid and aqueous solution phases, DFT calculations were combined with Pulay’s scaled quantum mechanics force field methodology in order to fit the theoretical wavenumber values to the experimental ones. In this way, a complete assignment of all the observed bands in the infrared spectrum for l-ascorbic acid was performed. The natural bond orbital study reveals the characteristics of the electronic delocalization of the three structures while the corresponding topological properties of electronic charge density are analyzed by employing Bader’s atoms-in-molecules theory.
Fil: Bichara, Laura Cecilia. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Física; Argentina
Fil: Lanús, Hernán Enrique. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Física; Argentina
Fil: Nieto Peñalver, Carlos Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Planta Piloto de Procesos Industriales Microbiológicos; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Microbiología; Argentina
Fil: Brandan, Silvia Antonia. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Física; Argentina
Materia
Ascorbic
Molecular-Force-Field
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/41494
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Density Functional Theory Calculations of the Molecular Force Field of l -Ascorbic Acid, Vitamin CBichara, Laura CeciliaLanús, Hernán EnriqueNieto Peñalver, Carlos GabrielBrandan, Silvia AntoniaAscorbicMolecular-Force-Fieldhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1We have studied l-ascorbic acid and characterized it by infrared spectroscopy in solid and aqueous solution phases. The density functional theory (DFT) method together with Pople’s basis set show that three stable molecules for the compound have been theoretically determined in the gas phase, and that an average of only two more stable conformations are present in the solid phase, as it was experimentally observed. The harmonic vibrational wavenumbers for the optimized geometries of both structures were calculated at B3LYP/6-31G*and B3LYP/6-311++G** levels at the proximity of the isolated molecule. For a complete assignment of the vibrational spectra in the compound solid and aqueous solution phases, DFT calculations were combined with Pulay’s scaled quantum mechanics force field methodology in order to fit the theoretical wavenumber values to the experimental ones. In this way, a complete assignment of all the observed bands in the infrared spectrum for l-ascorbic acid was performed. The natural bond orbital study reveals the characteristics of the electronic delocalization of the three structures while the corresponding topological properties of electronic charge density are analyzed by employing Bader’s atoms-in-molecules theory.Fil: Bichara, Laura Cecilia. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Física; ArgentinaFil: Lanús, Hernán Enrique. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Física; ArgentinaFil: Nieto Peñalver, Carlos Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Planta Piloto de Procesos Industriales Microbiológicos; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Microbiología; ArgentinaFil: Brandan, Silvia Antonia. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Física; ArgentinaAmerican Chemical Society2010-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/41494Bichara, Laura Cecilia; Lanús, Hernán Enrique; Nieto Peñalver, Carlos Gabriel; Brandan, Silvia Antonia; Density Functional Theory Calculations of the Molecular Force Field of l -Ascorbic Acid, Vitamin C; American Chemical Society; Journal of Physical Chemistry A; 114; 14; 4-2010; 4997-50041089-5639CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/jp912251ginfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/abs/10.1021/jp912251ginfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:05:33Zoai:ri.conicet.gov.ar:11336/41494instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:05:33.629CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Density Functional Theory Calculations of the Molecular Force Field of l -Ascorbic Acid, Vitamin C
title Density Functional Theory Calculations of the Molecular Force Field of l -Ascorbic Acid, Vitamin C
spellingShingle Density Functional Theory Calculations of the Molecular Force Field of l -Ascorbic Acid, Vitamin C
Bichara, Laura Cecilia
Ascorbic
Molecular-Force-Field
title_short Density Functional Theory Calculations of the Molecular Force Field of l -Ascorbic Acid, Vitamin C
title_full Density Functional Theory Calculations of the Molecular Force Field of l -Ascorbic Acid, Vitamin C
title_fullStr Density Functional Theory Calculations of the Molecular Force Field of l -Ascorbic Acid, Vitamin C
title_full_unstemmed Density Functional Theory Calculations of the Molecular Force Field of l -Ascorbic Acid, Vitamin C
title_sort Density Functional Theory Calculations of the Molecular Force Field of l -Ascorbic Acid, Vitamin C
dc.creator.none.fl_str_mv Bichara, Laura Cecilia
Lanús, Hernán Enrique
Nieto Peñalver, Carlos Gabriel
Brandan, Silvia Antonia
author Bichara, Laura Cecilia
author_facet Bichara, Laura Cecilia
Lanús, Hernán Enrique
Nieto Peñalver, Carlos Gabriel
Brandan, Silvia Antonia
author_role author
author2 Lanús, Hernán Enrique
Nieto Peñalver, Carlos Gabriel
Brandan, Silvia Antonia
author2_role author
author
author
dc.subject.none.fl_str_mv Ascorbic
Molecular-Force-Field
topic Ascorbic
Molecular-Force-Field
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv We have studied l-ascorbic acid and characterized it by infrared spectroscopy in solid and aqueous solution phases. The density functional theory (DFT) method together with Pople’s basis set show that three stable molecules for the compound have been theoretically determined in the gas phase, and that an average of only two more stable conformations are present in the solid phase, as it was experimentally observed. The harmonic vibrational wavenumbers for the optimized geometries of both structures were calculated at B3LYP/6-31G*and B3LYP/6-311++G** levels at the proximity of the isolated molecule. For a complete assignment of the vibrational spectra in the compound solid and aqueous solution phases, DFT calculations were combined with Pulay’s scaled quantum mechanics force field methodology in order to fit the theoretical wavenumber values to the experimental ones. In this way, a complete assignment of all the observed bands in the infrared spectrum for l-ascorbic acid was performed. The natural bond orbital study reveals the characteristics of the electronic delocalization of the three structures while the corresponding topological properties of electronic charge density are analyzed by employing Bader’s atoms-in-molecules theory.
Fil: Bichara, Laura Cecilia. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Física; Argentina
Fil: Lanús, Hernán Enrique. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Física; Argentina
Fil: Nieto Peñalver, Carlos Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Planta Piloto de Procesos Industriales Microbiológicos; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Microbiología; Argentina
Fil: Brandan, Silvia Antonia. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Física; Argentina
description We have studied l-ascorbic acid and characterized it by infrared spectroscopy in solid and aqueous solution phases. The density functional theory (DFT) method together with Pople’s basis set show that three stable molecules for the compound have been theoretically determined in the gas phase, and that an average of only two more stable conformations are present in the solid phase, as it was experimentally observed. The harmonic vibrational wavenumbers for the optimized geometries of both structures were calculated at B3LYP/6-31G*and B3LYP/6-311++G** levels at the proximity of the isolated molecule. For a complete assignment of the vibrational spectra in the compound solid and aqueous solution phases, DFT calculations were combined with Pulay’s scaled quantum mechanics force field methodology in order to fit the theoretical wavenumber values to the experimental ones. In this way, a complete assignment of all the observed bands in the infrared spectrum for l-ascorbic acid was performed. The natural bond orbital study reveals the characteristics of the electronic delocalization of the three structures while the corresponding topological properties of electronic charge density are analyzed by employing Bader’s atoms-in-molecules theory.
publishDate 2010
dc.date.none.fl_str_mv 2010-04
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/41494
Bichara, Laura Cecilia; Lanús, Hernán Enrique; Nieto Peñalver, Carlos Gabriel; Brandan, Silvia Antonia; Density Functional Theory Calculations of the Molecular Force Field of l -Ascorbic Acid, Vitamin C; American Chemical Society; Journal of Physical Chemistry A; 114; 14; 4-2010; 4997-5004
1089-5639
CONICET Digital
CONICET
url http://hdl.handle.net/11336/41494
identifier_str_mv Bichara, Laura Cecilia; Lanús, Hernán Enrique; Nieto Peñalver, Carlos Gabriel; Brandan, Silvia Antonia; Density Functional Theory Calculations of the Molecular Force Field of l -Ascorbic Acid, Vitamin C; American Chemical Society; Journal of Physical Chemistry A; 114; 14; 4-2010; 4997-5004
1089-5639
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/jp912251g
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/abs/10.1021/jp912251g
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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